Since the first isolation of a crystalline N-heterocyclic carbene (NHC), NHCs are widely employed as ligands in organometallic chemistry, organocatalysts, and Lewis bases for the stabilization of reactive main-group species. Applications of NHCs have been significantly furthered by the advent of multifunctional NHCs by the introduction of substituents on either the nitrogen atom(s) or on the backbone of the NHCs. Recently, we have developed N-phosphine oxide-substituted imidazolylidenes (PoxIms) through the direct introduction of the phosphoryl group onto the nitrogen atom, which can work as a Lewis base and an electrophile showing multipurpose utility. Herein, we report the phosphorylation of CO2 to afford carboxylic-phosphinic mixed anhydrides by using PoxIms, demonstrating a novel application of multifunctional NHC in organic synthesis. Furthermore, this method extended to phosphorylation of isocyanates and aldehydes.

Phosphorylation of carbon-oxygen bond mediated by N-phosphine oxide-substituted imidazolylidenes

2019 Fall National Meeting

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